Preparation, Electronic and Liquid Crystalline Properties of Electron-Accepting Azaacene Derivatives

Takashi Takeda; Tomohiro Ikemoto; Shunsuke Yamamoto; Wakana Matsuda; Shu Seki; Masaya Mitsuishi; Tomoyuki Akutagawa

doi:10.1021/acsomega.8b01943

Preparation, Electronic and Liquid Crystalline Properties of Electron-Accepting Azaacene Derivatives

ACS Omega. 2018 Oct 19;3(10):13694-13703. doi: 10.1021/acsomega.8b01943. eCollection 2018 Oct 31.

Authors

Takashi Takeda^{1

2}, Tomohiro Ikemoto², Shunsuke Yamamoto^{1

2}, Wakana Matsuda³, Shu Seki³, Masaya Mitsuishi^{1

2}, Tomoyuki Akutagawa^{1

2}

Affiliations

¹ Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Sendai, Miyagi 980-8577, Japan.
² Department of Applied Chemistry, Graduate School of Engineering, Tohoku University, Sendai, Miyagi 980-8579, Japan.
³ Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Kyoto, Kyoto 615-8520, Japan.

Abstract

A series of electron-accepting azaacene-type materials 1-4 with different kinds and degrees of intermolecular interactions were synthesized. Simple modification of the terminal substituents significantly modulated the photophysical and electrochemical properties. The degree of weak intermolecular interaction determined the emergence of a liquid crystalline (LC) phase for each compound. Dipole-dipole interaction, π-π interaction, and van der Waals interaction all contributed to stabilize the LC phase of 1 and 2. The introduction of strong hydrogen bonding interaction enabled the formation of a highly ordered LC phase in 4. Charge-transport properties of 1, 2, and 4 were also investigated.